Development of a Pilot-Plant Process for a Nevirapine Analogue HIV NNRT Inhibitor
Organic Process Research & Development2008Vol. 12(4), pp. 603–613
Citations Over TimeTop 19% of 2008 papers
Carl A. Busacca, Mike Cerreta, Yong Qiang Dong, Magnus Eriksson, Vittorio Farina, XuWu Feng, Jiyoung Kim, Jon C. Lorenz, Max Sarvestani, Robert E. Simpson, Rich Varsolona, Jana Vitous, Scot Campbell, Mark S. Davis, Paul‐James Jones, Daniel L. Norwood, Fenghe Qiu, Pierre L. Beaulieu, Jean‐Simon Duceppe, Bruno Haché, Jim Brong, Fang-Ting Chiu, Tom Curtis, Jason Kelley, Young S. Lo, Tory H. Powner
Abstract
The pilot-plant synthesis of nevirapine analogue 1 is described. The compound was prepared in eight steps from substituted pyridine raw materials and 4-hydroxyquinoline. The key transformation involves a novel one-pot conversion of an arylhalide to arylacetic acid under palladium catalysis, followed by regioselective reduction via in situ generated BH3/THF to the arylethanol intermediate 2. All stages were carried out on 10−150-kg scale.
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